Conformational requirements of a stereospecific three-to five-carbon ring expansion reaction

Tetrahedron Letters

Volumn 37, Issue 9, 1996, Pages 1359-1362

  Hill, David K ^a   Herndon, James W ^a  

^a Bldg 142   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOALKENE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0029875165     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00022-6     Document Type: Article

References (15)

1. Piers, E.; Compehensive Organic Synthesis; Trost, B., Ed.; Pergamon Press: New York; 1991, Vol. 5, Chapter 8.2, pp. 971.
2. Rhoads, S. J.; Raulins, N. R. Org. React. 1975, 22, 1.
3. a. Baldwin, J. E.; Ullenius, J. E. J. Am. Chem. Soc. 1974, 96, 1542.
4. b. Baldwin, J. E.; Gilbert, K. E. J. Am. Chem. Soc. 1976, 98, 8283.
5. c. Davies, H. M. L.; Clark, T. J.; Smith, H. D. J. Org. Chem. 1991, 56, 3817.
6. d. Harvey, D. F.; Lund, K. P. J. Am. Chem. Soc. 1991, 113, 5066.
7. Herndon, J. W.; McMullen, L. A. J. Am. Chem. Soc. 1989, 111, 6854.
8. Herndon, J. W.; Hill, D. K.; McMullen, L. A. Tetrahedron Lett. 1995, 36, 5687.
9. 2, m/z 268.1463).
10. a. Casey, C. P.; Shusterman, A. J. Organometallics 1985, 4, 736.
11. b. Arvarez, C.; Pacreau, A.; Parlier, A.; Rudler, H.; Daran, J.-C. Organometallics 1987, 6, 1057.
12. For similar Cope-like rearrangements of Organometallics, see: a. Casey, C. P.; Vosejpka, P. C.; Underiner, T. L.; Slough, G. A.; Gavney, J. A. Jr. J. Am. Chem. Soc. 1993, 115, 6680.
13. b. Trost, B. M.; Dyker, G.; Kulawiec, R. J. J. Am. Chem. Soc. 1990, 112, 7809.
14. The allyl ligand has a low migratory aptitude in CO insertion reactions, while alkenyl/aryl ligands are similar to alkyl ligands. a. Green, M.; Craig, P. J. J. Chem. Soc. pt. A; 1969, 157.
15. For a review, see Wojcicki, A. Adv. Organometal. Chem. 1972, 11, 88.